137553-93-6Relevant academic research and scientific papers
A TRANSKETOLASE-BASED SYNTHESIS OF (+)-exo-BREVICOMIN
Myles, David C.,Andrulis, Peter J.,Whitesides, George M.
, p. 4835 - 4838 (1991)
The naturally occuring beetle pheromone (+)-exo-brevicomin was synthesized by a strategy combining chemical and enzymatic steps.The commercially available enzyme transketolase (EC 2.2.1.1) catalyzed the condensation of β-hydroxypyruvic acid and 2-hydroxybutyraldehyde to furnish the central intermediate in the sequence, optically active hydroxyketone 5.A short sequence converted ketose 5 to protected aldose 8.Wittig extension of the aldehyde followed by hydrogenation and ketal hydrolysis generated the title compound.
Synthesis of β,γ-disubstituted-γ-lactones through a Johnson-Claisen rearrangement: a short route to xylobovide, nor-canadensolide, canadensolide, sporothriolide and santolinolide
Fernandes, Rodney A.,Ingle, Arun B.,Chavan, Vijay P.
, p. 2835 - 2844 (2009)
The Johnson-Claisen rearrangement of allyl alcohols with chiral vicinal diol functionality was employed to access chiral β,γ-disubstituted-γ-lactones in high enantio- and diastereoselectivity. These were efficiently converted into nor-canadensolide, the advanced γ-(lactone-lactol) intermediate for xylobovide, canadensolide and sporothriolide and the lactone moiety of the santolinolides.
A novel and stereospecific synthesis of (+)-exo-brevicomin
Raghavan, Sadagopan,Joseph, Suju C.
, p. 8237 - 8239 (2007/10/03)
A novel and stereospecific synthesis of (+)-exo-brevicomin is disclosed. The key step of the reaction sequence employs the sulfinyl moiety as an intramolecular nucleophile to functionalize an alkene π-complexed to a bromonium ion.
